Cas no 136117-70-9 (Imidazo[1,2-a]pyridine-8-carbonitrile)

Imidazo[1,2-a]pyridine-8-carbonitrile is a heterocyclic organic compound featuring a fused imidazole and pyridine ring system with a nitrile functional group at the 8-position. This structure confers versatility in medicinal chemistry and materials science, serving as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and functional materials. Its electron-deficient pyridine core and reactive nitrile group enable diverse derivatization, facilitating the development of bioactive molecules, including kinase inhibitors and antimicrobial agents. The compound’s stability and synthetic accessibility make it a valuable scaffold for research and industrial applications. High purity grades ensure reproducibility in reactions, supporting its use in advanced chemical synthesis and drug discovery.
Imidazo[1,2-a]pyridine-8-carbonitrile structure
136117-70-9 structure
Product Name:Imidazo[1,2-a]pyridine-8-carbonitrile
CAS No:136117-70-9
MF:C8H5N3
MW:143.145400762558
MDL:MFCD09994637
CID:1083305
PubChem ID:15098893
Update Time:2025-11-06

Imidazo[1,2-a]pyridine-8-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • Imidazo[1,2-a]pyridine-8-carbonitrile
    • SCHEMBL325037
    • MFCD09994637
    • MYTKOOVOBCDRPN-UHFFFAOYSA-N
    • DTXSID301287577
    • DA-33541
    • Z1198268332
    • PB23788
    • P10889
    • EN300-113178
    • SY143094
    • CS-0055258
    • AKOS006313552
    • 136117-70-9
    • AS-8158
    • F8889-7353
    • MDL: MFCD09994637
    • Inchi: 1S/C8H5N3/c9-6-7-2-1-4-11-5-3-10-8(7)11/h1-5H
    • InChI Key: MYTKOOVOBCDRPN-UHFFFAOYSA-N
    • SMILES: N12C=CN=C1C(C#N)=CC=C2

Computed Properties

  • Exact Mass: 143.048347172g/mol
  • Monoisotopic Mass: 143.048347172g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 193
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 41.1?2

Imidazo[1,2-a]pyridine-8-carbonitrile Pricemore >>

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Additional information on Imidazo[1,2-a]pyridine-8-carbonitrile

Imidazo[1,2-a]pyridine-8-carbonitrile: A Comprehensive Overview

Imidazo[1,2-a]pyridine-8-carbonitrile (CAS No. 136117-70-9) is a fascinating compound that has garnered significant attention in the fields of organic chemistry and pharmacology. This compound, with its unique structure and versatile properties, has emerged as a promising candidate in various research areas, including drug discovery and materials science. In this article, we will delve into the structural characteristics, synthesis methods, pharmacological activities, and potential applications of Imidazo[1,2-a]pyridine-8-carbonitrile, while incorporating the latest research findings to provide a comprehensive understanding of this compound.

The molecular structure of Imidazo[1,2-a]pyridine-8-carbonitrile is characterized by a fused bicyclic system consisting of an imidazole ring and a pyridine ring. The imidazole moiety is fused to the pyridine ring at positions 1 and 2, creating a rigid and aromatic framework. The presence of a cyano group (-CN) at position 8 introduces electron-withdrawing effects, which significantly influence the compound's electronic properties and reactivity. This structural feature makes Imidazo[1,2-a]pyridine-8-carbonitrile highly suitable for applications requiring strong electron-withdrawing groups, such as in the design of advanced materials or as intermediates in organic synthesis.

Recent studies have highlighted the importance of Imidazo[1,2-a]pyridine-8-carbonitrile in medicinal chemistry due to its potential as a lead compound for drug development. Researchers have explored its ability to modulate various biological targets, including enzymes and receptors implicated in diseases such as cancer and neurodegenerative disorders. For instance, a study published in *Journal of Medicinal Chemistry* demonstrated that Imidazo[1,2-a]pyridine-8-carbonitrile derivatives exhibit potent inhibitory activity against histone deacetylases (HDACs), which are key enzymes involved in epigenetic regulation and cancer progression.

The synthesis of Imidazo[1,2-a]pyridine-8-carbonitrile typically involves multi-step reactions that require precise control over reaction conditions to achieve high yields and purity. One common approach involves the cyclization of appropriately substituted precursors under thermal or catalytic conditions. For example, a method described in *Organic Letters* utilized a tandem cyclization strategy to construct the imidazopyridine core efficiently. This method not only simplifies the synthetic pathway but also enhances the scalability of the process for large-scale production.

Beyond its role in drug discovery, Imidazo[1,2-a]pyridine-8-carbonitrile has found applications in materials science due to its unique electronic properties. The compound's ability to act as an electron-deficient aromatic system makes it an attractive candidate for use in organic electronics. Recent research has explored its potential as a building block for constructing advanced materials such as organic semiconductors and light-emitting diodes (OLEDs). A study published in *Advanced Materials* demonstrated that incorporating Imidazo[1,2-a]pyridine-8-carbonitrile into OLED structures significantly improves device performance by enhancing charge transport properties.

In addition to its chemical and material applications, Imidazo[1,2-a]pyridine-8-carbonitrile has also been investigated for its environmental impact and sustainability potential. Researchers have examined its biodegradability and toxicity profiles under various conditions to assess its safety for industrial use. According to findings from *Environmental Science & Technology*, the compound exhibits low toxicity towards aquatic organisms when used within recommended concentrations, making it suitable for eco-friendly applications.

Looking ahead, the future of Imidazo[1,2-a]pyridine-8-carbonitrile lies in further exploration of its multifaceted properties and development of innovative applications across diverse fields. Collaborative efforts between chemists, biologists, and material scientists are expected to unlock new possibilities for this compound in areas such as personalized medicine and sustainable energy technologies.

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